WO2012059585A1 - Procédé d'élaboration de n-(benzyl)cyclopropanamines substitués par hydrogénation d'imines - Google Patents

Procédé d'élaboration de n-(benzyl)cyclopropanamines substitués par hydrogénation d'imines Download PDF

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Publication number
WO2012059585A1
WO2012059585A1 PCT/EP2011/069426 EP2011069426W WO2012059585A1 WO 2012059585 A1 WO2012059585 A1 WO 2012059585A1 EP 2011069426 W EP2011069426 W EP 2011069426W WO 2012059585 A1 WO2012059585 A1 WO 2012059585A1
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Prior art keywords
alkyl
different halogen
halogen atoms
carbonyl
alkoxy
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PCT/EP2011/069426
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English (en)
Inventor
Norbert Lui
Wahed Ahmed Moradi
Thomas Norbert MÜLLER
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Bayer Cropscience Ag
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Filing date
Publication date
Priority to EP11778894.3A priority Critical patent/EP2635551B1/fr
Priority to ES11778894.3T priority patent/ES2680546T3/es
Priority to BR112013010990-4A priority patent/BR112013010990B1/pt
Priority to US13/883,241 priority patent/US9260378B2/en
Priority to DK11778894.3T priority patent/DK2635551T3/en
Priority to KR1020137014336A priority patent/KR101874659B1/ko
Application filed by Bayer Cropscience Ag filed Critical Bayer Cropscience Ag
Priority to MX2013004881A priority patent/MX2013004881A/es
Priority to JP2013537149A priority patent/JP2014503481A/ja
Priority to CN201180053177.2A priority patent/CN103402970B/zh
Priority to MX2015006719A priority patent/MX364906B/es
Publication of WO2012059585A1 publication Critical patent/WO2012059585A1/fr
Priority to IL226132A priority patent/IL226132B/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
    • C07C209/52—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of imines or imino-ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
    • C07C211/35—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing only non-condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
    • C07C217/58—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/04—Formation of amino groups in compounds containing carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
    • C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

Definitions

  • the present invention relates to a process for the preparation of substituted N-(benzyl)cyclopropanamines of the general formula (II) starting from N-[(aryl)methylene]cyclopropanamine derivatives.
  • the present invention further provides the N-[(aryl)methylene]cyclopropanamine derivatives used as starting compounds in this process according to the invention and also their use for the preparation of substituted N-(benzyl)cyclopropanamines.
  • N-(benzyl)cyclopropanamines are important intermediates for the manufacture of agrochemical active ingredients.
  • Correspondingly substituted N-(benzyl)cyclopropanamines are described, for example, in the synthesis of fungicidally effective pyrazolecarboxamides (cf. e.g.. WO 2007/087906, PCT/EP2010/056521). It is known that N- (phenylmethylene)cyclopropanamine can be reduced with sodium cyanoborohydride to give N-benzyl- cyclopropanamine (see J. Lab. Comp. Radiop arm. 1981, 18, 781-90 and J. Org. C em. 2000, 65, 96-103).
  • a disadvantage of this process is high costs of sodium cyanoborohydride.
  • sodium triacetoxyboro- hydride is used instead of sodium cyanoborohydride.
  • Synthetic Commun. 2003, 33, 3419-3425 only borohydride in methanol is used.
  • the costs are too high.
  • a further process the alkylation of cyclopropylamine with benzyl bromide, is described in Bioorg. Med. Chem. 2006, 14, 8506-8518. Here, the yield following complex chromatography is only 48%. In the case alkylation with benzyl bromide, the possible polyalkylation also takes place.
  • Tetrahedron 2008, 64, 11783-11788 describes the preparation of N-monosubstituted benzylamines with hydrogen and palladium on carbon in chloroform. This gives the hydrochloride.
  • a disadvantage of this process is the use of toxic chloroform and corrosion problems on account of the acidic hydrogenation.
  • the hydrogenolysis of cyclopropyl groups to the corresponding n-propyl or isopropyl derivatives in the presence of hydrogenation catalysts even under mild conditions is generally known and adequately described (cf.
  • the object of the present invention is to provide an alternative process for the preparation of substituted N-(benzyl)cyclopropanamines which can preferably be carried out easily and cost- effectively.
  • the substituted N-(benzyl)cyclopropanamines obtainable using this desired process should preferably be obtained with high yield and high purity.
  • the desired process should allow the desired tar- get compounds to be obtained without the need for complex purification methods.
  • This object is achieved by a novel process for the preparation of substituted N-(benzyl)cyclopropanamines.
  • Z is hydrogen, Ci-Cg-alkyl, Ci-C 4 -haloalkyl or C 3 -C 7 -cycloalkyl,
  • X is halogen, cyano, hydroxyl, Ci-Cg-alkyl, Ci-Cg-haloalkyl having up to 9 identical or different halogen atoms, Ci-Cg-alkylamino, di(Ci-Cg-alkyl)amino, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy having up to 9 identical or different halogen atoms, Ci-Cg-alkoxy-Ci-Cg-alkyl; Ci-Cg-alkylsulphanyl, Ci-Cg-haloalkylsulphanyl having up to 9 identical or different halogen atoms, C 3 -C 7 -cycloalkyl, (C 3 -C7-cycloalkyl)-Ci-Cg-alkyl, C 3 -C 7 - halocycloalkyl having up to 9 identical or different halogen atom, formyl, formyloxy, formylamino, carboxy,
  • substituents X can form a 5- or 6-membered ring, which may be saturated or unsaturated and optionally also comprises heteroatoms,
  • n 1, 2, 3, 4 or 5
  • Z is preferably hydrogen, methyl, ethyl, propyl or isopropyl.
  • X is preferably halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl having up to 9 identical or different halogen atoms,
  • Ci-Cg-alkoxy Ci-Cg-haloalkoxy having up to 9 identical or different halogen atoms, carboxy, C 3 -C 7 - cycloalkyl or tri(Ci-Cg-alkyl)silyl.
  • two substituents X preferably form a 5- or 6-membered ring, as a result of which a bicycle selected from 1,3-benzodioxolyl, 1,2,3,4-tetrahydroquinoxalinyl, 3,4-dihydro-2H-l,4-benzoxazinyl, 1,4- benzodioxanyl, indanyl, 2,3-dihydrobenzofuranyl or indolinyl is formed,
  • n is preferably 1. 2 or 3.
  • Z is particularly preferably hydrogen, methyl.
  • X is particularly preferably fluorine, chlorine, methyl, ethyl, propyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy, trimethylsilyl, carboxy.
  • n is particularly preferably 1 or 2.
  • Z is very particularly preferably hydrogen.
  • X is very particularly preferably fluorine, chlorine, methyl, methoxy, isopropyl, tert-butyl, trifluoromethyl, trifluoromethoxy, trimethylsilyl, carboxy.
  • n is very particularly preferably 1.
  • the desired substituted N-(benzyl)cyclopropanamines of the general formula (II) are prepared by a catalytic hydrogenation of the corresponding N-[(aryl) methylene] cyclo- propanamine derivatives of the general formula (I).
  • the desired substituted N-(benzyl)cyclopropanamines of the general formula (II) are obtained under the preferred reaction conditions according to the invention and specified in more detail below, with good yields in high purity, the process according to the invention thus overcoming the disadvantages specified above.
  • the desired compounds are obtained here in a purity which generally renders extensive work-up of the direct reaction product unnecessary.
  • alkyl either on its own or in combination with further terms such as, for example, haloalkyl, is understood as meaning a radical of a saturated, aliphatic hydrocarbon group having 1 to 8 carbon atoms, which may be branched or unbranched.
  • Ci-Cg-alkyl radicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, n-hexyl n-heptyl and n-octyl. From these alkyl radicals, Ci-C 6 -alkyl radicals are particularly preferred. Ci-C 4 -alkyl radicals are especially preferred.
  • aryl is understood as meaning an aromatic radical having 6 to 14 carbon atoms, preferably phenyl.
  • halogen substituted by halogen are understood as meaning, for example, haloalkyl, radicals halogenated one or more times up to the maximum possible number of substitu- ents.
  • the halogen atoms may be identical or different.
  • Halogen here stands for fluorine, chlorine, bromine or iodine, in particular for fluorine, chlorine or bromine.
  • alkoxy either on its own or in combination with further terms such as, for example, haloalkoxy, is in the present case understood as meaning a radical O-alkyl, the term “alkyl” having the meaning above.
  • Optionally substituted radicals may be mono- or polysubstituted, where, in the case of a polysubstitution, the substituents may be identical or different.
  • the conversion of the N-[(aryl)methylene]cyclopropanamine derivatives of the general formula (I) to the corresponding amines of the general formula (II) is carried out by a catalytic hydrogenation [Process (A)].
  • the catalyst which may be used for the catalytic hydrogenation for reducing the compound of the general formula (I) is any desired hydrogenation catalyst.
  • Suitable catalysts optionally comprise one or more metals of groups 8 - 10 of the Periodic Table of the Elements on an arbitrary customarily inorganic support. Of suitability are, for example, precious metal catalysts, such as ruthenium catalysts, palladium catalysts, platinum catalysts and rhodium catalysts, Raney nickel catalysts and Raney cobalt and Lindlar catalysts.
  • the corresponding catalysts can be used in supported form, for example on carbon (carbon or activated carbon). Aluminium oxide, silicon dioxide, zirconium dioxide, calcium carbonate or titanium dioxide. Corresponding catalysts are known per se to the person skilled in the art. Particular preference is given to palladium catalysts. The catalysts can be used either in their damp form or dry form. The catalyst used is preferably reused for several reactions.
  • the catalyst is used in a concentration of from about 0.01 to abut 30% by weight, based on the imine of the formula (I) used.
  • the catalyst is used in a concentration o from about 0.01 to about 5% by weight, particularly preferably from about 0.1 to about 2.0% by weight.
  • the catalytic hydrogenation can be carried out under superatmospheric pressure in an autoclave or at atmospheric pressure in a hydrogen gas atmosphere.
  • the hydrogen gas atmosphere can additionally also comprise inert gases, for example argon or nitrogen.
  • the catalytic hydrogenation is carried out preferably at a temperature of form 10 to 200°C, particularly preferably at 10 to 150°C, very particularly preferably at 10 to 60°C.
  • the hydrogen pressure is usually 0.1 to 50 bar, preferably 0.1 to 30 bar, particularly preferably 1 to 6 bar.
  • Solvents are advantageously used in an amount such that the reaction mixture remains readily stirrable throughout the entire hydrogenation process.
  • Suitable solvents for carrying out the process according to the invention are all organic solvents that are inert under the reaction conditions, the type of solvent used depending on the way in which the reduction is carried out.
  • alcohols such as methanol, ethanol, isopropanol, butanol
  • ethers such as ethyl propyl ether, methyl tert-butyl ether, «-butyl ether, anisole, phenetol, cyclohexyl methyl ether, dimethyl ether, diethyl ether, dimethyl glycol diphenyl ether, dipropyl ether, diisopropyl ether, di- «-butyl ether, diisobutyl ether, diisoamyl ether, ethylene glycol dimethyl ether, isopropyl ethyl ether, tetrahydrofuran, methyl tetrahydro- furan, dioxane, dichlorodiethyl ether and polyethers of ethylene oxide and/or propylene oxide; amines such as trimethyl-, triethyl-, tripropyl-, tributylamine
  • reaction according to the invention as in process (A) can also be carried out without a diluent for N-[(aryl)methylene]cyclopropylamine derivatives of the formula (I) that are present in liquid form.
  • solvent amounts used when carrying out the process (A) according to the invention can be varied within a wide range.
  • solvent amounts in the range from 1 times to 50 times the amount of solvent, particularly preferably from 2 times to 40 times the amount of solvent, in particular from 2 times to 30 times the amount of solvent, in each case based on the N-[(aryl)methylene]cyclopropanamine derivative of the general formula (I) used, are used.
  • the present invention also relates to the use of the compounds of the formula (I) for the preparation of compounds of the general formula (II), as is disclosed in the process described above.
  • the present invention also provides a process (B) for the preparation of the N-[(aryl)methylene]cyclopropanamine derivatives of the general formula (I)
  • an acid can optionally be added as catalyst.
  • examples thereof are acetic acid, p-toluolenesulphonic acid, trifluoroacetic acid.
  • Acetic acid is preferably used.
  • Acidic salts can also be used, e.g. KHS0 4 or NaHS0 4 .
  • corresponding catalysts are used, then their amount can be from 0.01 to 10 percent by weight, based on the cyclopropylamine used.
  • process (B) can also be carried out such that the water which is formed during the reaction between amine and carbonyl compound of the formula (III) by condensation is removed from the reaction mixture.
  • water-binding agents for example sodium sulphate, magnesium sulphate or molecular sieve, or by using a device for separating off water.
  • the hydrogenation can, however, also be carried out without removal of the water.
  • Process (B) can generally be carried out under reduced pressure, at atmospheric pressure or under superatmos- pheric pressure.
  • the temperatures used can likewise vary, depending on the substrates used, and are easy for the person skilled in the art to ascertain through routine experiments.
  • the reaction for the preparation of the compounds of the general formula (I) can be carried out at a temperature of -20°C to 200°C, preferably 10 to 100°C. Particular preference is given to carrying out the reaction at atmospheric pressure and temperatures of 10 to 100°C.
  • process (B) can also be carried out in the presence of solvents (diluents). The solvents are also used in this process step preferably in an amount such that the reaction mixture remains readily stirrable throughout the entire process.
  • Suitable solvents for carrying out the process according to the invention for the preparation of the imines of the general formula (I) are all organic solvents that are inert under the reaction conditions. Examples are: alcohols such as methanol, ethanol, isopropanol, butanol; ethers, such as ethyl propyl ether, methyl tert-butyl ether, «-butyl ether, anisole, phenetol, cyclohexyl methyl ether, dimethyl ether, diethyl ether, dimethyl glycol diphenyl ether, dipropyl ether, diisopropyl ether, di- «-butyl ether, diisobutyl ether, diisoamyl ether, ethylene glycol dimethyl ether, isopropyl ethyl ether, tetrahydrofuran, dioxane, dichlorodiethyl ether and polyethers of ethylene oxide and/or propylene oxide
  • reaction between amine and the carbonyl compound of the formula (III) can also take place without a diluent.
  • process (B) is carried out in a solvent
  • the solvent can be removed by distillation after the end of the reaction. This can take place under atmospheric pressure or reduced pressure at room temperature or elevated tempera- tures.
  • the mixture can also be transferred directly to the hydrogenation, which is advantageous particularly from the point of view of economic considerations.
  • a work-up of the imine of the formula (I) is then dispensed with.
  • the present invention further provides the N-[(aryl)methylene]cyclopropanamine derivative of the general formula (I)
  • the reaction was carried out on a 0.072 molar scale. The hydrogen absorption was complete after five hours. The desired product was obtained in 80.4% yield.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

La présente invention concerne un procédé pour élaborer des N-(benzyl)cyclopropanamines substituées représentées par la formule générale (II) à partir de dérivés de N-[(aryl)méthylène]cyclopropanamine. L'invention concerne également des dérivés de N-[(aryl)méthylène]cyclopropanamine utilisés comme composés de départ pour le procédé selon l'invention, et leur utilisation pour l'élaboration de N-(benzyl)cyclopropanamines substitués.
PCT/EP2011/069426 2010-11-05 2011-11-04 Procédé d'élaboration de n-(benzyl)cyclopropanamines substitués par hydrogénation d'imines WO2012059585A1 (fr)

Priority Applications (11)

Application Number Priority Date Filing Date Title
ES11778894.3T ES2680546T3 (es) 2010-11-05 2011-11-04 Procedimiento de preparación de N-(bencil)ciclopropanaminas sustituidas por hidrogenación de imina
BR112013010990-4A BR112013010990B1 (pt) 2010-11-05 2011-11-04 Processo para a preparação de n-(benzil)ciclopropanaminas, processo para a preparaçãodos derivados de n-[(aril)metileno]ciclopropanamina e derivados de n-[(aril)metileno]ciclopropanamina
US13/883,241 US9260378B2 (en) 2010-11-05 2011-11-04 Process for the preparation of substituted N-(benzyl)cyclopropanamines by imine hydrogenation
DK11778894.3T DK2635551T3 (en) 2010-11-05 2011-11-04 PROCEDURE FOR THE PREPARATION OF SUBSTITUTED N- (BENZYL) CYCLOPROPANAMINES USING IMINHYDRATION
KR1020137014336A KR101874659B1 (ko) 2010-11-05 2011-11-04 이민 수소화로써의 치환된 ｎ-(벤질)시클로프로판아민의 제조 방법
EP11778894.3A EP2635551B1 (fr) 2010-11-05 2011-11-04 Procédé d'élaboration de n-(benzyl)cyclopropanamines substitués par hydrogénation d'imines
MX2013004881A MX2013004881A (es) 2010-11-05 2011-11-04 Proceso para la preparacion de n-(bencil)ciclopropanaminas sustituidas mediante hidrogenacion de iminas.
JP2013537149A JP2014503481A (ja) 2010-11-05 2011-11-04 イミン水素化による置換ｎ−（ベンジル）シクロプロパンアミンの調製方法
CN201180053177.2A CN103402970B (zh) 2010-11-05 2011-11-04 通过亚胺氢化制备取代的n‑(苄基)环丙胺的方法
MX2015006719A MX364906B (es) 2010-11-05 2011-11-04 Proceso para la preparacion de n-(bencil) ciclopropanaminas sustituidas mediante hidrogenacion de iminas.
IL226132A IL226132B (en) 2010-11-05 2013-05-02 A process for the preparation of n-(benzyl)cyclopropaneamines converted by imine hydrogenation

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US41051710P 2010-11-05 2010-11-05
EP10190077 2010-11-05
US61/410,517 2010-11-05
EP10190077.7 2010-11-05

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WO2012059585A1 true WO2012059585A1 (fr) 2012-05-10

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PCT/EP2011/069426 WO2012059585A1 (fr) 2010-11-05 2011-11-04 Procédé d'élaboration de n-(benzyl)cyclopropanamines substitués par hydrogénation d'imines

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US (1) US9260378B2 (fr)
EP (1) EP2635551B1 (fr)
JP (1) JP2014503481A (fr)
KR (1) KR101874659B1 (fr)
CN (1) CN103402970B (fr)
BR (1) BR112013010990B1 (fr)
DK (1) DK2635551T3 (fr)
ES (1) ES2680546T3 (fr)
IL (1) IL226132B (fr)
MX (1) MX2013004881A (fr)
TW (2) TWI562977B (fr)
WO (1) WO2012059585A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9440908B2 (en) 2012-04-26 2016-09-13 Bayer Cropscience Ag Process for preparing N-(5-chloro-2-isopropylbenzyl)cyclopropanamine

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2016143737A1 (ja) * 2015-03-11 2017-12-28 三菱瓦斯化学株式会社 新規ポリアミン化合物及びその製造方法、並びに、及びこれを用いたエポキシ樹脂用硬化剤、エポキシ樹脂組成物及びエポキシ樹脂硬化物
JP6711104B2 (ja) * 2015-04-24 2020-06-17 Jsr株式会社 レジスト下層膜形成方法及びパターン形成方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006066896A2 (fr) 2004-12-23 2006-06-29 Novartis Ag Composes organiques
WO2007087906A1 (fr) 2006-02-01 2007-08-09 Bayer Cropscience Sa Dérivés fongicides de n-cycloalkyl-benzylamide
WO2008033456A1 (fr) * 2006-09-15 2008-03-20 Schering Corporation Dérivés d'azétidine spiro-condensés convenant pour le traitement de la douleur, du diabète et des troubles du métabolisme des lipides
EP2119703A1 (fr) * 2007-01-15 2009-11-18 Santen Pharmaceutical Co., Ltd Nouveau dérivé d'indole ayant une activité inhibitrice sur la i b kinase

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3083226A (en) * 1961-10-18 1963-03-26 Abbott Lab N-benzyl cyclopropylamines and carbamates
US3153093A (en) * 1961-11-22 1964-10-13 Abbott Lab Amino derivatives of nu-cyclopropylbenzylamines
US6252090B1 (en) * 2000-08-29 2001-06-26 Allergan Sales, Inc. Compounds having activity as inhibitors of cytochrome P450RAI
WO2004033418A2 (fr) 2002-10-11 2004-04-22 Actelion Pharmaceuticals Ltd. Derives d'acide sulfonylamino-acetique
EP2061792A2 (fr) 2006-09-15 2009-05-27 Schering Corporation Dérivés d'azétidinone et procédés d'utilisation de ceux-ci
CN102015606B (zh) * 2007-06-08 2015-02-04 满康德股份有限公司 IRE-1α抑制剂
CA2722734C (fr) * 2008-05-05 2013-11-05 Merck Frosst Canada Ltd. Derives de piperidine substitues en 3,4 utilises en tant qu'inhibiteurs de la renine
KR102085535B1 (ko) * 2012-04-26 2020-03-06 바이엘 크롭사이언스 악티엔게젤샤프트 Ｎ-(5-클로로-2-이소프로필벤질)시클로프로판아민의 제조 방법

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006066896A2 (fr) 2004-12-23 2006-06-29 Novartis Ag Composes organiques
WO2007087906A1 (fr) 2006-02-01 2007-08-09 Bayer Cropscience Sa Dérivés fongicides de n-cycloalkyl-benzylamide
WO2008033456A1 (fr) * 2006-09-15 2008-03-20 Schering Corporation Dérivés d'azétidine spiro-condensés convenant pour le traitement de la douleur, du diabète et des troubles du métabolisme des lipides
EP2119703A1 (fr) * 2007-01-15 2009-11-18 Santen Pharmaceutical Co., Ltd Nouveau dérivé d'indole ayant une activité inhibitrice sur la i b kinase

Non-Patent Citations (16)

* Cited by examiner, † Cited by third party
Title
A. D. DILMAN ET AL: "Trifluoromethylation of salicyl aldimines", JOURNAL OF ORGANIC CHEMISTRY., vol. 72, no. 22, 2007, USAMERICAN CHEMICAL SOCIETY, WASHINGTON, DC., pages 8604 - 8607, XP002631590, ISSN: 0022-3263 *
BIOORG. MED CHEM., vol. 14, 2006, pages 8506 - 8518
BOWMAN W R ET AL: "GENERATION OF AMINYL RADICALS USING SULFENAMIDES AS SYNTHETIC PRECURSORS", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 50, no. 4, 1 January 1994 (1994-01-01), pages 1275 - 1294, XP002046441, ISSN: 0040-4020, DOI: DOI:10.1016/S0040-4020(01)80837-1 *
CHEM. EUR. J, vol. 3, 1997, pages 1370 - 1374
H. T. NAGASAWA ET AL: "Latent inhibitors of aldehyde dehydrogenase as alcohol deterrent agents", JOURNAL OF MEDICINAL CHEMISTRY., vol. 27, no. 10, 1984, USAMERICAN CHEMICAL SOCIETY. WASHINGTON., pages 1335 - 1339, XP002631589, ISSN: 0022-2623 *
HARADA, THE CHEMISTRY OF THE CARBON-NITROGEN DOUBLE BOND, pages 276 - 293
J LAB. COMP. RADIOPHARM., vol. 18, 1981, pages 781 - 90
J ORG. CHEM., vol. 65, 2000, pages 96 - 103
K. VUKICS ET AL: "Synthesis of C-aryl-N-cyclopropylnitrones", SYNTHETIC COMMUNICATIONS., vol. 33, no. 19, 2003, TAYLOR & FRANCIS GROUP, pages 3419 - 3425, XP002631591, ISSN: 0039-7911 *
NISHIMURA: "Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis", 2001, JOHN WILEY & SONS, pages: 640 - 647
NISHIMURA: "Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis2", 2001, JOHN WILEY AND SONS, pages: 226 - 250
RYLANDER: "Catalytic Hydrogenation in Organic Syntheses", 1979, ACADEMIC PRESS, pages: 251 - 259
RYLANDER: "Catalytic Hydrogenation over Platinum Metals", 1967, ACADEMIC PRESS, pages: 291 - 303
SYNTHETIC COMMUN., vol. 33, 2003, pages 3419 - 3425
TETRAHEDRON, vol. 64, 2008, pages 11783 - 11788
TRIPATHI R P ET AL: "Synthesis and antitubercular activity of substituted phenylmethyl- and pyridylmethyl amines", BIOORGANIC & MEDICINAL CHEMISTRY, PERGAMON, GB, vol. 14, no. 24, 15 December 2006 (2006-12-15), pages 8186 - 8196, XP025133654, ISSN: 0968-0896, [retrieved on 20061215], DOI: DOI:10.1016/J.BMC.2006.09.020 *

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US9440908B2 (en) 2012-04-26 2016-09-13 Bayer Cropscience Ag Process for preparing N-(5-chloro-2-isopropylbenzyl)cyclopropanamine

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